Hydrogen Bromide → 4-(2-bromoacetyl)benzoic Acid

Participants

Reaction Conditions

Reaction Steps

2.0 g (12.2 mmole) of 4-acetyl benzoic acid was added to 90 ml of acetic acid in a 500 ml erlenmeyer flask and heated at 45° C. until dissolved. Maintaining the temperature at 45° C., 1.95 g (12.2 mmole, 0.61 ml) of bromine dissolved in ~2 ml acetic acid was added slowly over 1 hour with vigorous stirring. The reaction required an induction period of several minutes before proceeding, which became evident by the loss of the red bromine color and the evolution of HBr. The product, BABA (Modifying Reagent II), was precipitated on ice, collected by filtration and recrystallized 3 times from hot (75° C.) ethanol.

Provenance & Evidence